Patent GB-1377190-A (GB)
Title: Water-soluble fibre-reactive azo dyestuffs
IPC: C09B62/507
Filed: 1971-11-04
Abstract: 1377190 Phenyl ureas and carbamates containing sulphone groups FARBWERKE HOECHST AG 4 Nov 1971 [4 Nov 1970] 51328/71 Headings C2C and C2P [Also in Division C4]  N - (3 - Amino - 4 - sulphophenyl) - N<SP>1</SP> - (3- # - chloroethylsulphonyl - phenyl) - urea is prepared by condensing 1,3-diaminobenzene-4- sulphonic acid (I) with 3-(#-chloroethylsulphonyl) phenyl isocyanate; N-(3-amino-4-sulphophenyl) - N<SP>1</SP> - (3 - vinylsulphonylphenyl) - urea and N - [4<SP>1</SP> - amino - 3<SP>1 </SP>- sulpho - diphenyl (4)]- N<SP>1</SP> - (4 - # - chloroethylsulphonylphenyl) - urea are similarly prepared. N - (3 - Amino - 4 - sulphophenyl) - N<SP>1</SP> - (4 - # - sulphatoethylsulphonylphenyl)-urea is prepared by (1) condensing 4-aminophenyl-(#-sulphatoethyl)-sulphone (II) with phenyl chloroformate to give N-(4-#-sulphatoethylsulphonylphenyl)- carbamic acid phenyl ester and reacting this with (I) or (2) reacting (I) first with phenyl chloroformate and then with (II); N-(3-#-chloroethylsulphonylphenyl)-carbamic acid phenyl ester, N- (4 - sulpho - 3 - aminophenyl) - N<SP>1</SP> - (3 - # - chloroethylsulphonylphenyl) - urea, N - (4 - amino - 3- sulphophenyl) - N<SP>1</SP> - (4 - # - thiosulphatoethyl- - phenyl) - urea, N - (3 - # - hydroxyethyl sulphonyl phenyl)-carbamic acid phenyl ester, N-(4- sulpho - 3 - aminophenyl) - N<SP>1</SP> - (3 - # - hydroxyethylsulphonylphenyl)- urea, N - (4 - # - phosphatoethylsulphonylphenyl) - carbamic acid phenyl ester and N - (4 - sulpho - 3 - aminophenyl)- N<SP>1</SP> - (4 - # - phosphatoethylsulphonylethylphenyl)- urea are similarly prepared. N - (4 - Carboxy - 3 - aminophenyl) - N<SP>1</SP> - (3- # - chloroethylsulphonylphenyl)-urea is prepared by condensing 2-nitro-4-aminobenzoic acid with 3 - # - chloroethylsulphonyl - phenyl - isocyanate to give. N - (4 - carboxy - 3 - nitrophenyl) - N<SP>1</SP>- (3 - # - chloroethylsulphonylphenyl)-urea which is catalytically hydrogenated; 4-amino-2,2<SP>1</SP>-disulpho - 4<SP>1</SP>- (4 - # - chloroethylsulphonylphenyl). ureido - stilbene, N - ethyl - N - (3 - aminophenyl)- N<SP>1</SP> - (4 - # - chloroethylsulphonylphenyl) - urea, N - methyl - N - (4 - nitrophenyl) - N<SP>1</SP> - (4 - #- sulphatoethylsulphonylphenyl)-urea, N-(4-sulpho- 3 - aminophenyl) - N<SP>1</SP> - (3 - # - thiosulphatoethylsulphonylphenyl)-urea, N - (4 - nitro- or -amino- 3 - sulphophenyl) - N<SP>1</SP> - (4 - # - sulphatoethylsulphonylphenyl) - urea, N - (4 - sulpho - 3- nitro- or -amino-phenyl) - N<SP>1</SP> - (4 - # - hydroxyethylsulphonylphenyl) - urea and N - (4 - nitro- or -amino - 3 - sulphophenyl) - N<SP>1</SP> - (4 - # - phosphatoethylsulphonylphenyl)-urea are similarly prepared. N - (4 - Sulpho - 3 - aminophenyl) - N<SP>1</SP> - (3- # - thiosulphatoethylsulphonylphenyl) - urea is prepared by reacting the corresponding vinylsulphonyl or chloroethylsulphonyl compound with Na thiosulphate. N - (4 - Sulpho - 3 - aminophenyl) - N<SP>1</SP> - (3 - #- diethylaminoethylsulphonylphenyl) - urea is prepared by reacting the corresponding vinylsulphone with diethylamine. N - (4 - Sulpho - 3 - nitrophenyl) carbamic acid phenyl ester is prepared by condensing 3-nitro-4- sulpho-aniline with phenyl chloroformate.